Synthesis, XRD/HSA-interactions, synthon, TD-DFT/optical analysis, docking and antibacterial evaluation of two (±)-Isoflavonoid derivatives

Abstract

A high-yield synthesis of the new racemic (±)-2-(1-bromoethyl)-7‑methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one was achieved in two steps by O- and 2-C-methylation 7,4′-dihydroxy-2-methylisoflavone, followed by radical bromination of the allylic methylene moiety using N-bromosuccinimide. XRD-crystallography, NMR, UV–vis CHN-EA, and FT-IR were all used to establish the identity and structure of the target ligand. Both the XRD, Hirshfeld surface area (HSA) and the DFT structural optimization validated the (±)‑bromo-chromen-4-one structural formula. XRD analysis reveals two types of synthons due to the presence of multiple short interactions, including CMe-H.....Br/Cph-H.....O and H…πCC. There is a high harmony between the experimental XRD-structural parameters and their DFT counterparts; additionally, the optical characteristics were derived by comparing the experimental UV–Vis result to the TD-DFT/B3LYP and TD-DFT/CAM-B3LYP ones. The compounds capacity to bind to DNA was assessed via the molecular docking technique with the use of 1BNA. The antibacterial activity of the produced (±)‑bromo-chroman-4-one and (±)-the non bromo‑chroman-4-one derivatives was evaluated against eight bacterial strains.